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Ammonium Chloride → 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide

HRID 1962886
Notes
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Reaction equation

HRID 1962886 reaction equation
[NH2:1][C:2]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3]1.[CH3:8]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH4+].[Cl-].[C:32]([C:34]1[CH:35]=[N:36][C:37]2[C:42]([CH:43]=1)=[CH:41][C:40]([O:44][C:45](C)([SH:49])[C:46](O)=[O:47])=[CH:39][CH:38]=2)#[CH:33]>CC#N.CCN(CC)CC>[C:32]([C:34]1[CH:35]=[N:36][C:37]2[C:42]([CH:43]=1)=[CH:41][C:40]([O:44][CH:45]([S:49][CH3:8])[C:46]([NH:1][C:2]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3]1)=[O:47])=[CH:39][CH:38]=2)#[CH:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21624254(1-Aminocyclobutyl)methanolHCID 86647257(3-Ethynyl-quinolin-6-yloxy)-methyl sulfanyl-acetic acid

Product 1

HCID 595653282-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

To a mixture containing (1-amino-cyclobutyl)-methanol (preparation described in JP 08134044) (860 mg), aza-HOBT (600 mg), TBTU (1.41 g) and Et3N (1 ml) in CH3CN (30 ml), (3-ethynyl-quinolin-6-yloxy)-methyl sulfanyl-acetic acid dissolved in Et3N (1 ml) and CH3CN (30 ml) was added over 1 hr, at room temperature, under nitrogen atmosphere. The resulting brown suspension was stirred overnight at room temperature then poured into aq NH4Cl solution and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 1/3) to give 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide (1.09 g) as slightly yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over sodium sulphate anhydrous
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 1/3)

Sources & evidence

ORD record
ord-b5b2c18d0d9542fd91d48f0de30f6f26
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415272B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes